How do VCs make money?

I’ve written a little bit before about how venture capitalists (VCs) make money (see this post).

But I’ve never quite spelled it out, and in this post I’ll do just that. I think it’s useful to understand this — certainly for anyone who is an aspiring future VC — but even for entrepreneurs, because it helps to understand the mindset of people you’re pitching.  

What is a Venture Capitalist (VC)?

At a high level, the concept of a VC is relatively straightforward — a VC is basically a middle (wo)man.  On one side, a VC will raise money from rich people called Limited Partners (LPs). These can be individuals, families, corporations, and other funds who invest in funds, etc. VCs then take that money and on the other side, invest in startups. The hope is that some subset of those startups will grow tremendously, and then through some sort of liquidity event — it could be an acquisition or an IPO or even a way to sell shares to someone else in a secondary sale, the VC will receive back a lot more cash than initially invested.  That cash then gets returned back to the initial investors and the VC makes some money in between. 

Typical VC structure

A very common lifespan of a VC fund in the US is 10 years.  In other countries, this varies quite a bit — in China, for example, VC funds have been set up to be closer to a 5 year time horizon.  

The term is largely based on how long it will take to get liquidity on deals. Investors who invest in such a fund are committed to locking up their capital for 10 years. Now throughout the 10 years, it’s possible that investors may receive capital back from exits that happened before 10 years, but the bulk of the great exits will happen closer to the 10 year mark. For reference, Dropbox went IPO after 15 years, and so if you were an early stage investor, you would’ve made a lot of money, but that may not have happened for many years.

Side note: it is possible with the new Long Term Stock Exchange (LTSE) coming to fruition, we may see early stage VCs shorten their time horizons to getting liquidity.  The bar to have a successful IPO on the NYSE and the NASDAQ has been raised considerably since the 90s, so companies have been staying private for much longer. If you look back at Amazon’s IPO in the 1990s, their valuation was pegged just over $400m. These days, Uber went public at over $80B valuation!  If we enable more liquidity events at earlier stages, it’s possible we may see changes in fund lifespans.

In the US, a typical VC firm economics structure follows a 2% / 20% rule.  The 2% rate represents management fees. And the 20% represents something called carry.

What are management fees?

Management fees are basically the operating budget for a VC firm on an annual basis.  So in a 2% model, if you have a $10M fund, you have a $200,000 budget every year for the course of your fund.

If you have a $100m fund, with a 2% structure, you’d have an annual operating budget of $2 million each year. So as you can see, there is a stark difference in budget between a microfund and a large Sand Hill VC. And when people talk about VCs having nice salaries, they are referring to partners and employees who work at the latter type of firm — firms with a lot of money under management. Microfunds are very much like bootstrapped startups.

Let’s dive into the economics of a $10m fund. The $200,000 budget needs to cover just about everything.  Certainly, it includes salaries, but it also needs to include other things like marketing expenses, health insurance and travel. If you have an office, that must fit under this budget too. And so if your typical microfund has two partners, they are definitely earning well under $100,000 per year, and more likely closer to $50,000 given that all expenses must fit under this $200,000 number.  For us at Hustle Fund, in our 3 person partnership, we have publicly stated that we currently each make close to $50k per year and feel lucky to be able to bootstrap for a while.

What is carry?

The 20% represents the profit sharing of a VC fund. The way profits are distributed look something like this:

Say a $10m fund returns $20m. The initial $10m is first returned to the Limited Partners (LPs).  Then the $10m profit is returned such that the fund managers receive 20% of this profit, or $2M (the yellow shape) in this example.  That $2m is then distributed to the employees / partners of the fund based on however they’ve all mutually agreed to do so. (At Hustle Fund, all 3 partners have equal carry).   And, the LPs receive the rest – $8M in this example, and so the LPs receive a total of $18m in this example (the blue shape).

Even though the fund returned 2x at a gross level, after all is distributed, LPs see a net multiple of 1.8x, because of the carry.  

Screen Shot 2019-06-06 at 3.08.36 PM.png

The power law of startups

Ok, now let’s look at the investing side. The interesting thing about the investing side is that startup outcomes are distributed very much in line with the power law. Namely, most startups will fail and will go to zero — i.e. you will lose your money entirely.  Some will maybe return 2x or more. And if you have an excellent portfolio, you will capture a 100x-1000x returning company once in a while.

In order to succeed at investing in startups, you absolutely need at least one of these outliers in order to be successful. I hear all these non-investors or new investors talk about trying to find 3x multiples in startups. If you are investing at the early stages, you need to be aiming for much higher than that…  

I put together this spreadsheet of startup outcomes that everyone can copy, so you can all play with the numbers.

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Let’s look at the tab labeled “1 – 100x return”. If we assume the trite saying that 9/10 startups fail, and let’s say we have one big winner that delivers 100x returns, you can see that we can return an overall nice fund — 8x gross multiple, 6.6x net multiple to LPs.  From this, you can see that it doesn’t matter that we have really low survivability in the portfolio. All that matters is that your one big winner was quite big.

Dilution impacts your returns as an early stage investor

Now, let’s add the impact of dilution back into this equation.  Typically, a cap table will get diluted down by 10-30% each round, with an average being around 20%.  Assuming that we are the earliest stage investors, this means that if a founder does 3 rounds of funding after ours, we will be diluted down by about 50%!  So I modeled out the 100x winner as 50x in the next tab. You can see we are still returning good returns but if you aren’t aiming for 100x gross difference between your entry point and exit point in your investments, things start to get a bit dicey.  

Can you improve survivability?

There’s a lot of debate amongst VCs about whether the 9/10 survivability that everyone touts is actually accurate. Can you help your companies survive longer so that you have more winners?  


I personally think the answer is yes, but I think you still need at least one big winner to make the portfolio work out well. If we look at the tab labeled “5 – 3x returns”.  You can see that even if we do phenomenally well with picking startups who have high survivability, if they are not returning much, our multiple on our fund is just barely over 1x and the net to LPs is basically that they get their money back.  Wait, what is going on? There are a lot of 3x returners!

Screen Shot 2019-06-07 at 2.17.21 PM.png

The primary reason for this is the management fees.  Even though this VC fund isn’t making money off management fees — heck their budget is only $200k per year, on a $10m fund, $2m in total is used for management fees. In other words, this money isn’t being invested.  So only $8m is invested, and so you have to overcome this initial hurdle to get to 1x. A lesser reason is once you cross the 1x hurdle, carry digs into some of the profits. (Side note: most VCs recycle small exits in order to invest more than 80% of their fund, but getting money back to recycle is not guaranteed and for the purpose of simplification, I removed that scenario.)

To be clear, this isn’t a situation that the managers of the fund want either.  They are taking a puny salary of like $50k per year. And their profits are only $400k after 10 years of work that gets divided across the partnership — this is really dinky.

So you can play with the numbers on this spreadsheet, but you’ll find that even if you can increase survivability, you still need to be aiming for big winners.  

How do you get a big winner?

Now, what does it mean to get a 100x returner? This means that if we invest at say $3m post money valuation, and the company sells for $300m, the difference in entry point and exit point is 100x. (Accounting for 3 rounds of dilution, this will be closer to a 50x returner).  

Think about it — $300m is a big exit. It’s more than life-changing for most entrepreneurs. And many entrepreneurs might be tempted to sell even sooner.  Heck $30m for most people is life changing. Remember, as a VC, we are the middle (wo)man, so we need that exit to be large for us to make a lot of money. But the entrepreneur doesn’t need a large exit to make good money. So there’s a bit of a disconnect there.  

Large multiples occur when there’s a large spread between entry point valuation and exit valuation. VCs all have different strategies to achieve this. Some like to go in at low valuations and then sell for sub billion dollar exits.  And this works, because there are many more exits that are sub $1B. And then there are VCs who have the exact opposite strategy. Entry point doesn’t matter, but they are gunning for an exit at a multi-billion dollar valuation. For example, Uber’s IPO was approximately at $80B valuation. If you got in at $5m valuation, then that’s on the order of a 10,000x multiple after accounting for dilution. So with that kind of exit, who cares if you got in at the $5m valuation or the $10m valuation or even higher — it’s all a wash at that scale.

But regardless of the strategy, all VCs aim to have large multiples.

You can also see that VCs can do VERY well if they end up getting a few 100x winners.  Play with the spreadsheet — even with just one more 100x winner on the first spreadsheet, you can see that the net fund outcome to LPs goes up to 13x. So, a $100k investment into a fund turns into a million dollar outcome.  On the flip side, more 3x outcomes on the last spreadsheet with near perfect survivability in a portfolio isn’t that awesome.


Based on all of this, this explains why VCs:

  • May be valuation sensitive (depending on the strategy)
  • Are only looking for super large outcomes and don’t care about good businesses
  • Often pattern match — if they believe that “certain types of founders” can get funding easily, then they may have an easier time growing super large companies (I don’t believe in this personally, but this explains this behavior)
  • Are looking for fast growth — winners must get to a billion dollar level within just a few years since a VC fund term is 10 years
  • Fight over pro-rata — dilution can be rough so maintaining ownership in companies that are clearly strong winners is helpful to returns
  • Don’t care about massive failures and would much prefer even just 1 “go big or go home” outcome to one that will be successful at a $50m outcome level.

I think following the money is always a good way to understand why people behave the way that they do. Hopefully these spreadsheets help to understand how VCs make their money. 

15 Annoying Things that VCs say or ask (and how to think about them)

Today’s blog post is all about the annoying things that VCs commonly say or ask.  I did a call out on Twitter this week and these are the VCisms that the crowds have bubbled up as the most annoying things out of a VC’s mouth.

1) What if Google Builds It?  (@pravesh)

This one was cited a LOT by many people on Twitter in various forms! There were variations — e.g. substitute Google with Amazon or Facebook or any other big company.

Admittedly it’s a valid question — what if the 800 lb gorilla in your space does copy you? What is your edge? How will you win?

Here are a couple of answers that may help:

A. Large companies are so large, they aren’t able to prioritize or even care about your “small” opportunity relative to their huge company. In the case of Google specifically, it has actually been shown that building a Google product competitor can actually be a great opportunity.  Many people would much prefer to pay for products so that they can get customer support when something goes wrong — a free Google product will never a customer’s calls or emails.

Companies like Mixpanel, Optimizely, Superhuman, and many more have built big businesses by going head-to-head with a free Google product by charging customers and providing a better experience.

So it’s actually validation of your market if Google is interested in your space.

B. Big companies, by definition, are no longer nimble.  You, in contrast, are able to run circles around them.  Can you prove that you’re nimble by shipping quickly?  Can you show that customers love you more than Google?  These are concrete things that you can point to in your conversations with VCs.

2) We don’t invest in hardware (only to find out that they led a round for hardware) (@peterjcolbert)

This is an interesting one, because you see VCs deviate from their thesis sometimes.  (Every VC does it – we’ve done it too.).  VCs will often say they don’t invest in hardware.  Or ad revenue based models.  Or e-commerce.  Or in some geography.  And then you see a portfolio company on their website that is clearly in one of these categories.

You should just ask a VC about it directly.  

The reason for this is usually along one of these lines:

A. They used to invest in that category but are now over-indexed. Or they invested in that category previously as an angel or with a past fund. I.e. they used to make those investments but no longer do.

This is important to understand, because if the reason the firm is passing is that they are waiting for some liquidity on existing positions in your space, there could potentially still be an opening for an investment later.  This is rare, BUT possible – this has happened once to a company that I’ve backed before.

B. They are experimenting outside their thesis. E.g. They may not usually invest in South America, but they may make 1 investment to learn about the market. They may not invest in hardware, but may invest in 2 companies to learn about the space.

Unfortunately, if this is the case, you can try to hard to convince a VC to do more experimentation in that category, but because VCs have mandates — i.e. they have an agreement with their investors that they would focus on investing in certain categories / theses, they will likely not want to deviate *too* much from their thesis.  VCs are judged by their investors on whether they end up investing based on the strategy that they claimed they would.

C. They had a special relationship with the founder.

There is nothing you can do about this.  People back their friends all the time regardless of what they are building.

I think it’s easy to walk away fuming mad thinking that a firm is filled with hypocrites, but it’s worth just bringing up with a VC: “Hey you mentioned that you don’t do hardware, but I noticed on your website that you’ve invested in X.  Am curious how that fits your thesis?” You may not like the response and it may not change anything, but on rare occasion it may open a door for you.

3) I don’t think this can be a venture scale business. (@kirbywinfield)

I’m of two minds on this one.

A. There are a lot of companies who seek out venture funding who are actually NOT a good fit for VC investors.  Entrepreneurs should be aware of the return profile that VCs are looking for.  Loosely speaking, VCs are looking for a minimum of 100x return in the course of 5 years or so.  This comes out to achieving roughly $100m runrate within the next 5 years.  Is this what you want to do?

B. However, on the flip side, what ideas will be able to achieve $100m runrate in 5 years is tough to say. VCs often have preconceived notions above what can get to this level and what cannot — and they are often wrong. Companies that tend to get overlooked are in categories such as e-commerce, for example.  Are you selling a widget that will likely max out at $5m in sales per year?  Or are you the next Stitch Fix?

My advice here would be to first understand for yourself if you want to be growing a business that goes to $100m in annual revenue in 5 years (and the work / hiring that will be required to do so). And if so, what do you think that path looks like if everything goes well?  How will you get to $2m runrate this year and then more than double your sales each year thereafter?

And if the answer is that you don’t want to run this type of business, there are other avenues of funding.  Angel funding, crowdfunding, revenue-based financing are all good channels that are now rapidly growing.

4) But how will you manage being a mom AND running a startup? (@hustlefundvc)

Ugh.  Are we in the 21st century?  Move on from any VC who asks this.  It’s not worth it.

5) We’d be interested when we see a bit more traction. (@msuster

Ah, the classic ask for more traction.  Basically, the VC doesn’t have conviction right now, but maybe, just maybe, more traction would give him/her the conviction to do your deal.  The reality is that most investors can’t articulate what level of traction they would want to see in order to invest.  Obviously, if you earn $100m in the next 2 months, everyone will be onboard, but what if you get to $100k / mo runrate in the next year — is that interesting?  Well…it depends.  And unless you are an asshole or a fraudster, VCs always want to preserve optionality to see you in a year and check on your business.

So, although this is a frustrating response, the right way to play this is to triage investors quickly.  Put this VC in a “not interested” bucket. Continue to send him/your monthly investor updates, but you’re better off trying to find someone who has conviction today than trying to convince someone to get conviction — even with traction.  You just need to meet a lot of investors and triage a lot of investors quickly in order to find the right investors to bring into your company.

6) Maybe you should raise more and grow quicker. (@justinpushas)

This is just a stupid comment.  If a VC really believes in your business, he/she will commit to your round, and will either help you fill your larger round or write a bigger check.  But, investors who say things like this without any action are either just oblivious or not helpful, and should just move on from these investors. As we all know, founders who struggle to raise $250k are also going to have a tough time raising $2.5m.

That being said, I would recommend that every founder develop multiple fundraising plans.  This will allow you to pitch a different amount of money to bigger or smaller investors with different milestones and goals that you would achieve with different investment sizes. And then if you do receive this question, you can point to a larger fundraising plan and mention that you have thought about a larger plan and are open to raising more money but are also not limited in growth if you cannot raise that amount now.

7) Come back when you have a lead (@stefanopep3)

The herd of sheep comment!  A variation on this is, “I’m committed once you have a lead.” This is a positive way for a VC to say no for now, but if you have enough fundraising traction, then he/she wants to get his/her foot in the door.

It’s important to clarify what a VC means by this, though.  Does this mean he/she is interested: 

  • When you have most of your round committed?
  • Once terms have been set?
  • If another investor is taking a board seat and is providing “serious responsibility ” for the investment.  (i.e. no party rounds)?

This is important to clarify, because VCs mean different things when they ask about a lead VC. 

If it’s the former — come back when most of the round is committed — you can build your round in many different ways.  You can bring together a party round of smaller investors without a lead on a convertible note or SAFE.  It’s actually quite common these days for a smaller fund to set terms on a note or a SAFE and bring together a round that way.  

And if a VC is just looking to evaluate terms, then you can create your own terms on a note or a SAFE and present those to the VC. 

And lastly, if the VC is looking for a true “lead VC” to invest the majority of the round and take a board seat, etc, then this is a completely different ask from the prior two.

8) Let me know how I can help!  Founder asks for help. *crickets* (@quan)

When I started my VC career, I asked this question to a few entrepreneurs I met with.  I genuinely wanted to be helpful.  Then I quickly realized that there was literally nothing I could help with.  Hah.  Every founder just wanted investment dollars, and if I weren’t investing, I couldn’t even do introductions to other investors, because it would be a bad signal.

9) Nothing. They ghost you. (@ameetshah)


10) Contact us if you like but we prefer warm introductions. (@cwlucas)

I find this ironic — VCs prefer warm introductions, and YET, there are a lot of VC analysts who send outbound emails to startups completely cold asking to chat!

My recommendation here is to try to get a warm referral to a VC.  Just in general, it’s always better to have a common connection to build rapport with.  That being said, a lot of the newer VCs (esp microVCs) are ok with cold emails.  (For reference, 20% of our deals come in completely cold, and we see no difference in performance between the cohort of companies that came in cold vs warm)

My prediction in the next 5 years is that the VC world will move to largely accepting *good* cold emails.  Most cold emails are terrible and will likely be ignored, but you do have a shot if you can send a strong cold email.

11) (Live product, thousands of users) “Yes but what *traction* do you have?” 

(Gets in to YC) “Your valuation is so HIGH now!” (@kristentyrrell)

This is the typical Goldilocks and the 3 Bears problem.  At first, you’re “too early” — you don’t have enough traction.  And then, once you get there or another investor participates in your round and drives the valuation up, then you become “too late” — the valuation is too high.

As frustrating as this is, this is just a matter of luck / timing and fit.  As pre-seed investors, I am susceptible to this as well in some sense.  We invest really early (from a valuation perspective), so, by definition, we are not looking for traction.  This means that we make our decisions entirely based on gut instinct of the opportunity.  So, if we don’t have conviction in the business idea, we will pass. And once a founder proves with traction that we were wrong, we still won’t be able to invest, because the valuation will be too high.  That’s frustrating but I’d say frustrating for VCs who miss out too — as you may have seen from the Uber IPO, lots of VCs lost out on a lot of money, because they didn’t have conviction in the idea.

There’s a lot of gut instinct in this business, and to be honest, to be great at it, you only need to be right about 20-30% of the time.  It’s like baseball – you strike out most of the time.  If you were to work at any other job — imagine if you were say a surgeon — if you were right only 20-30% of the time, you would be fired and everyone would be dead.

Now, this doesn’t apply to multi-stage investors. If they miss out on your seed round, you can still re-approach them at the series A or the series B.

12) Why hasn’t this been done before? (@jacobshiach)

This is a seemingly ridiculous question, and it may also seem that a lazy VC may not want to do his/her own homework.  But, this question is meant to test how you think through trends and changes in your ecosystem.  If you believe that markets are efficient, your opportunity should not exist.  Why?  Because if it’s an obvious opportunity, it means that everyone would have done it already.

So what is your key insight or secret that enables you to know about this opportunity that others do not.  Is it your domain knowledge?  Is it that the opportunity is in between two sectors that most people are not familiar with?  Is it a behavioral trend that is happening to a certain demographic that you are a part of but most entrepreneurs are not?  Whatever it is, every startup needs to have a good answer for this.  Heck, even funds get asked this question — why aren’t other funds doing your strategy?  And I’d say, as annoying as it is, it’s a legit question.

13) How can this be a billion dollar company? (@rkorny)

You might wonder why VCs are so obsessed with billion dollar businesses.  This is because the economics of running a fund are so tough.  Basically, you have a bunch of portfolio companies that will completely fail.  So whatever 1-2 winners you have, will need to make up for that failure plus much more to return multiples for the fund.  (Read more here:

This means that VCs are looking for 100x+ multiple at a minimum on a successful company, and if they are coming into your round at the seed stage — say at $10m post money valuation, 100x on that is roughly a $1b exit not accounting for dilution.  So this comes back to the question from above — do you want to be raising money from VCs?  Is this the type of business you want to be running?

14) What’s the moat? (for a seed stage company) (@chloealpert)

This is super annoying for a seed stage company, because obviously there is no moat.

Thinking longer term, however, simplistically, there’s only one way to have a moat — and that is, your customers love you so much, they will never want to leave you and keep coming back.  There could be a lot of ways to build this — e.g. you have a better user experience / product, you have more data to make your solution better / more accurate, you have greater network effects and therefore have a better product, etc.  Depending on your idea, the way that you achieve this outcome will differ a lot.

VCs want to understand at scale, how you will achieve this.  This is especially key for companies that have commodity products — such as finance.  You don’t want to be competing on price or better deals, etc.  How will you build that better / smarter product?  How will you build that retention in business model?  VCs want to understand how you think about this 5 years from now more than what things look like today.

15) We’re going to pass but will be cheering for you from the sidelines. (@comaddox)

This is just a ridiculous phrase and pet peeve of mine.  What is this?  Bring It On?



Some thoughts on building wealth

Last week I gave a talk about wealth to students, and I thought that it would be worthwhile to share this here on my blog.

I’ve learned a lot about building wealth over the past 20 years (though am not wealthy yet!).  But, most of my learnings on wealth have come from observation of the people around me in just the last 5 years or so.

First off, I know that many people don’t care too much about money.  And that’s fine!  Many people have very noble missions in life.  But — wealth gives you power — the power to change things. To have influence. To put towards good causes. Whatever you want.

I’ve met so many people over the years who have said to me, “I don’t care about becoming rich – wealth doesn’t motivate me. What motivates me is ABC cause”.  And that may be true, but you need wealth to drive the things that do motivate you to really have an impact.

So, let’s talk about the general strategy to becoming wealthy. I think there are three stages:

  1. Saving money
  2. Investing in low-risk / low-return assets
  3. Investing in high-risk / high-return assets

Let’s dive into each of these stages.

Saving money

The first stage, I think, is obvious to many people.  When you don’t have any or much money, the best way to get started in building wealth is to save money. Some people are good at this. Other people are not good at this.  And people have different strategies on how to save money.  For example, my mom came to this country with just $25.  She and my grandparents were incredibly thrifty people.  One thing that both of my grandparents did was to have all their teeth extracted when they moved to America in order to reduce their dental expenses!  Other people have other strategies for amassing cash savings.  Some people get the highest paying job that they can. Other people don’t eat avocado toast. I think we all have different methods but in general, I think everyone understands that saving money is important in the very beginning.  

Investing in low-risk / low-return assets

The next stage of building wealth is about taking whatever savings you have and putting it into low-risk and low-returning assets. Because after all, you can’t really afford to lose your newly earned cash because you don’t have a lot of cushion.

Surprisingly, we don’t really learn anything in school about investing, which is an utter shame. Most people end up learning a little bit about investing from what they read online or places like Money magazine. Super low-risk and low-returning assets include things like government bonds, savings accounts, and even CDs.  For the most part, you won’t lose your money in these assets, but you won’t make any money either.   

A medium-risk / medium-return asset class that a lot of people know about are index funds — these are baskets of shares of public stocks.  Historically, index funds have returned about 2x over the course of a decade. In other words, if you put in $100 into the S&P 500, 10 years later, you might have about $200.  There is a lot of variation, however, in the returns depending on the year. For example, in 2018 alone, a typical index fund returned 20%. In other words, if you put $100 into an index fund in January 2018, by December, it was worth $120.  On the flip side, index funds also take a dive in value during recessions. In 2008/2009, the value of stocks dropped about 50% almost over night!  I call index funds medium-risk / medium-return asset classes, because unless the entire economy goes belly-up and the world ends, your money will likely not go completely to zero in the long run, because index funds are betting on the overall macro economy doing well.  And if that isn’t happening in the long run in the world, then we probably have much bigger problems on our hands — i.e. the world ending / we’re all going to die.

Investing in high-risk / high-return assets

I think the asset class that is talked about the least are the high-risk and high-return assets. There are a lot of these kinds of assets.  What I didn’t realize until my 30s was that the wealthiest people make their money on investments — these kinds of investments.  They don’t make money on their salary.  They don’t make money on their index funds.  This is something that most of mainstream America does not realize. 

There are many different types of high-risk / high-return assets, but what I want to focus on for this talk is the startup investment asset class.  There are many ways to invest in startups.  At the most hands-on level, you can build your own startup — invest your own time & money into your own company.  You can work for someone else’s startup or advise someone else’s startup.  You can invest directly into startups with just money.  You can invest in funds that invest in startups.  And at the most hands-off level, you can invest in funds that invest in funds that invest in startups.  All of these are risky — i.e. you may not see any return on your time or money at all.  Or, you can see a tremendous return.

I think many people think that to invest money into startups (whether directly or into a fund), you need to be super wealthy and as a result, they haven’t really thought about investing into this asset class.  For example, many years ago, a friend of mine was raising money for his fund.  He told me at a very high level about his new fund and wanted to understand my interest in learning more and potentially investing.  I immediately dismissed the idea. I didn’t even look into the opportunity, and I don’t even know what his strategy or thesis was.  This is because I believed I wasn’t wealthy enough to participate in such a high-risk, high-return asset class. I felt that I hadn’t accumulated enough cash to do this. Years later though, when I was raising money for Hustle Fund 1, I thought back on that memory and I realized that I had been wrong to immediately dismiss the opportunity.  It occurred to me that even though I don’t have a lot of wealth, there is always some amount that makes sense to participate with in a high-risk and high-return asset class.

For example, let’s say that hypothetically you have saved $100,000. And let’s say that you know you will not need to touch $25k of that money until after you retire but it’s not important to your retirement savings either.  In other words, you can afford to take quite a bit of risk with some subset of that $25k.  If you lost it all, that wouldn’t be fun, BUT is there an amount that you’d be willing to potentially lose entirely — to risk potentially achieving a 100x multiple on that investment?  E.g. would you be willing to risk $5K?  The likelihood of that $5k investment might go to zero but if in the off-chance it did well, it would turn into $500k. This is not some weird hypothetical.  As a concrete example, Uber has been in the news for their IPO.  A $5,000 investment into Uber at the seed stage would be worth $25M today! That’s life changing for most people, and it’s only a $5k risk. 


Image courtesy of Giphy

But, I don’t think most people think about their finances from a portfolio construction perspective.  I think most people fixate on saving money first and then *maybe* they buy a house or invest in index funds.  Most people never think about investing in high-risk / high-reward asset classes.  And these are the investments that are life changing and make people really wealthy.  Just to be clear, when I say “these”, I’m talking about high-risk / high-return assets, not necessarily angel investing, and there are all kinds of high-risk / high-return assets.  

Determining how much money to invest in a high-risk / high return asset class such as startups is really a matter of portfolio construction.  You would never want to risk all of your savings in this asset class. But there is some percentage that makes sense.  Maybe it’s just $1k.  Maybe it’s $5k.  Maybe it’s $25k.  Maybe it’s nothing right now but in 10 years, it could be $5k.  But most people just never think about this.  

This brings me to my next point. I think a lot of people think that angel investors deploy a lot of capital into startups.  Ten years ago, I used to think that angel investors typically invested $25k-$100k into each startup.  There are certainly angels at this level.  But what I’ve come to learn over the years that most people don’t talk about is that there are actually a LOT of angels who only deploy $1k or $5k or $10k into each company.  And if you think about it from that perspective, for most professionals, putting in $1K or $5K is actually not that big of a deal. Your bonus each year might cover your startup investing without needing to specifically save for investing in high risk / high return asset classes.

People ask me, “who are these startups who take $5k investments?”  It’s simple – most founders. But, you have to earn it. You have to be:

  • A fast decision maker — you are not putting in a lot of money, so your due diligence process has to be less than an investor with a larger check 
  • Not annoying / not a pain in the butt
  • Value add – there are lots of ways to be value-add even if you are not in the same industry nor know anything about startups; here are ways that anyone can help a company:
    • Provide feedback on a pitch deck
    • Provide feedback as a consumer on a user experience
    • Do introductions to other investors or potential hires

In fact, what most people don’t realize is that it’s generally easier to get into early stage fundraising rounds with just a small investment check.  If the round is oversubscribed, founders will consider adding a $5k investor if they think the person is worth it. It’s just an extra $5k of dilution.  No big deal. If you were investing $200k and the round is oversubscribed, you likely won’t get in because founders wouldn’t want to sell too much of their company.  If the round is undersubscribed, you can get into a round anyway at any amount.  

Now sometimes, there are minimum thresholds for investing.  For direct startup investing, this is often flexible, especially if the round is not oversubscribed.  But for funds, this isn’t true.  Part of the reason for this is that both startups and funds can only take on 99 accredited investors per SEC rules.  This means that if a VC fund is raising $100M dollars, the average investment check for each investor has to be over $1M each.  But, I wouldn’t let potential minimums deter you from looking into an opportunity whether it be startup investing or other high-risk / high-return assets.  

Investments beget investments

Once you start investing in startups in some fashion, there are all kinds of other benefits. You get to mingle with other investors.  These people are well-connected and can show you better deals, introduce you to other influential people, and help you out in so many ways.  Many angel investors fund other angel investors’ businesses.  This is partly why I know so many entrepreneurs who invest as small angels — even if they don’t have a lot of money — $1k or $5k investments here and there buy not only an investment but also a network.  The act of investing itself allows you to build rapport with other investors in an easy way.  And it doesn’t matter how much you’re investing. No one goes around saying how much they invested into a company. Just being an investor gives you benefits.

Rich people get richer

The last point is something that bothers me a little bit.  These days, there is a lot of talk about salaries – about how women, for example, don’t get paid as much as men for the same role. And I certainly think that’s an important problem to solve.  But what isn’t talked about at all, is that there are so few women investors. Making money on investments — above and beyond — makes way more money than any salary. But women are getting left behind because as a vast generalization, they don’t invest in high-risk / high-reward asset classes. If you had invested in Google at the seed round, you wouldn’t even care about working there. Investing can be life-changing as we’ve seen from the numbers above with the Uber IPO example.

When we started Hustle Fund, we pitched many of our friends, asking them to invest in our fund. It was a very eye opening experience. For many of our male friends whom we pitched, they saw Hustle Fund as a great opportunity. They saw all the upside potential of this fund and invested. When we tried to pitch female friends, almost all of them turned us down — in fact, most didn’t even want to hear the pitch! Now keep in mind, all of these people — both men and women — all worked in similar jobs and made similar amounts of money and had similar educational backgrounds.  But what was fascinating is that our  female friends didn’t see opportunity. They saw risk. They thought about all the things that could go wrong. They thought about losing their money. The differential between the number of male investors and female investors in our first fund is so huge that at our first LP meeting, one of my (few) female friends who invested commented “Where are all the women?”.  I didn’t have a good answer.

That made me think back to when my friend offered me the opportunity to invest in his fund and I didn’t even look at it. In retrospect, I absolutely should have looked at it and heard the pitch. And if I liked it, there would have been some amount that I would have offered to invest.  It may not have hit his minimum, but I should have looked into it.  This is a mindset shift that I’ve had over the years and one that I strongly believe that everyone should go through regardless of gender and demographic background.  For those of us who didn’t grow up in families that think in this way, it’s a hard mindshift, but one that I think is especially important for people who are not exposed to wealth.

People who do well on a high-risk / high-reward investments often take a good portion of those earnings and pour it into many more high-risk / high-reward investments, and the rich become richer.  A number of my friends who started out as small $5k angels here and there have gone on to make good money and pour that back into more investing.  And in just a short 10 years, they have done really well for themselves and are more than set for life.  Meanwhile, I’ve observed that my other friends who don’t do any of this high-risk / high-reward investing will likely get to the same point as these angel friends of mine in about another 40-80 years.  There are many different kinds of high-risk / high-reward assets, and I use startup investing as one example (that may or may not work for everyone), but I wanted to illuminate this overall asset profile (high-risk / high-return).  The difference between the group of people who invest in high-risk / high-return asset classes and those who don’t isn’t intelligence.  And it isn’t job function or salary.  It’s specific education around investing in high-risk / high-reward asset classes.  You will, of course, need to do your homework around specific opportunities in the latter and decide what makes sense, but thinking about your own portfolio management and how you bucket your money is the critical point.

So wrapping this all up, if there’s only a couple of things that you took away from this talk:

  • You make money from investing – not salaries. You don’t have to be a professional investor, but you should take cash from your job to invest in order to amass a lot of wealth.
  • Think about your own liquidity needs and start to move towards some riskier and higher reward investments as you amass more cash than you need.  Everyone will have a different amount that makes sense, but this is how you should be thinking about investing.
  • Start early — even as early as today.
  • If you don’t have an investment mindset, change it — regardless of what profession you are in. Your salary doesn’t make you wealthy.

And so as you go into the world and start to look for your first job and get to that first stage of amassing wealth, think about your plan for getting to the third stage.  Because amassing wealth gives you freedom and power to accomplish the mission that you actually want to tackle.

Go become wealthy and change the world!  Thank you for having me!

Disclaimer: This talk / blog post is not investment advice.  In case you are so inspired to run out and buy lottery tickets of any form – figuratively or literally, I encourage you to consult your financial advisor, your friends, your family, your dog and anyone else you trust on financial matters instead of relying on random blog posts such as this to make life changing decisions.  Thank you.

Thank you to Stonly Baptiste for his suggestions and feedback on this post!

On differentiation

Storytelling goes a long way in fundraising for your company.  One of the biggest components of this is differentiating your product / your company from others.

Differentiation is very difficult — there are so many entrepreneurs who are doing something similar to you and also so many alternatives that achieve the same results as your product / solution.  Even if no one has the exact same product as you, surely if you’re solving a problem, there is someone else providing a different means to the same end result.  And if there isn’t…are you really solving a problem?  So, differentiating your company well is tough.

So it’s important to think deeply about this.  Take the time to really hammer out a clear story on why your product / company is differentiated.  Here are a few areas entrepreneurs ought to think about differentiation:

1) Focus on results not features

The top way I see entrepreneurs differentiating their products is via features.  “Our UX is easier to use than the competition.  ABC product is so clunky.”   Or, “we have DEF feature but company XYZ doesn’t”.

Most of the time, features really don’t matter. Ultimately, consumers and businesses use products as a means to an end — they want to achieve X faster or cheaper or something.  It may be that your user interface makes it easier or faster to accomplish X.  But, people don’t care about what buttons your product has.  They care about that end result.  Focus your story around that.

Case in point: In the late 90s, Google was something like the 7th or 8th major search engine to emerge.  Their feature set was different from Yahoo’s — it was just one search box with nothing else on the screen.  Although UI was simple, that’s not why consumers switched their searches to Google.  That’s just a feature.  Consumers switched because they could get search results a LOT faster – orders of magnitude faster!  Consumers didn’t have to leave the computer to get a snack while waiting for their search results to load over their dial up modem connection!


Originally posted by archiemcphee

2) Your results should be 10x better than competitors or alternatives not incremental

This brings me to my next point.  When entrepreneurs do focus on presenting results, I find that they often tend to be incremental improvements.  In an investor’s eyes, incremental improvements are not interesting.  This is because incremental results are often not enough to get a consumer or a business to drop everything and make it a priority to switch from what they are already using to your product / solution.

In the case of Google, their results were not just a little bit better but an order of magnitude better.  E.g. Altavista seemed slightly faster than Yahoo (at least to me), but when Google came along, it was a no-brainer to use Google all the time.

Now, sometimes, you may need reframe your story here.  It’s not always possible for all your numbers to be an order of magnitude better.  You may need to pick a different result to differentiate on.  For example, let’s say you develop a new kind of airplane with less 2% less drag.  This, in itself, may be a small number.  But it could have an order of magnitude of effect on your gas costs for the plane or whatnot.  It’s important to think about what axis you want to compete on.

3) You may need to differentiate your company on something other than your product

This brings me to my next point.  Sometimes, it’s just not possible to compete at all on any numbers being an order of magnitude better.  Not all great products are an order of magnitude better.  And, that’s ok.  But, it means that you need to differentiate on something else.

You will also need to do this if you’re in an industry where people can’t look under the hood and believe that your results are actually better en mass.  For example: lead generation.  There are so many lead generation startups (I had one too!).  And they all say they provide awesome leads.  And they all say their leads are 10x more cost effective than everyone else.  How is this possible?  Who is telling the truth?  Probably everyone — for certain customers, specific lead generation platforms and services are better than others.  But it’s not possible for an investor to verify this en masse, so many investors will pass outright, because they don’t believe this differentiator is true and won’t be able to prove it.

For businesses like these where an investor cannot actually verify your differentiator, you will need to get creative in your story.  Usually, the best way to do this is to incorporate your personal story.  If you have unique insights or domain experience, maybe this is what you use to differentiate your company from others.  Don’t use a story that your competitors can use.  For example, in the lead generation industry, a story I hear all the time is about how “Martha runs a flower shop and didn’t have customers.  Then awesome lead gen platform ABC came in and got her customers.”  All of your competitors / alternatives are telling that same story.  Your story should be unique to you — a story that none of your competitors or alternatives can tell.

To come up with such a differentiated story, in many cases, you may want to make it about yourself or your personal insights that are unique.  What is interesting about you?  And why are *you* doing this lead generation business?  If you can’t think of anything, spend the time to think long and hard.

Here’s an example that a CEO gave me the other day.  He’s building a company in a vertical that is pretty crowded.  He said, “Let’s take a step back – before we dive into my business, I want to tell you a bit about my life.  My mom was a single mom.  And I grew up poor.  And I could not get into college.  And everyone wrote me off as a loser.  And so I had to take a job after high school to make ends meet.  And, I ended up in ABC industry taking the only job I could get.  From there, I did XYZ, and eventually I realized from working in this business that a) I wanted to prove myself – that I was not just this poor boy with no future.  And b) that I knew more about the ABC industry than most people in the world, and here are my insights on it. And this is why I’m starting this company.”

His story was incredibly compelling.  Even though his product insights were not unique, he was able to differentiate his company from many of the other ones I’ve heard pitch, because I believed he knew more than other people about this industry.

4) Think about future differentiation

Once you’ve established why your company / product is different, think about how you’ll continue to be different.  Investors call this your moat.  You don’t need it now — most companies are not really defensible when they first start — but investors want to know how you think about this and how you’ll work towards this.

Your strongest story will be about how you’ll continue to keep your company ahead of the pack.  For example, if you have data that feeds into your algorithms to make them stronger, then your story is about growing your data access so that you’ll continue to improve your algorithms.  If your story is about network effects of people on your platform, tout that story.

But there are a lot of stories about improving your product that I hear from entrepreneurs that are pretty weak.  Saying, for example, you’ll continue to improve the user experience on your platform, while may be true and important, is NOT compelling.  Investors would expect you to continue to improve the product, and any newcomers or future competitors would do the same.  Your head start is likely minimal, so it’s moot.  Any competitor can come in and build a better product than you or play catch up with a better UI.

In most cases, where you don’t have network effects in your product or viral loops or whatnot — and most companies don’t — you’ll need to tell a story about a thesis that you have.  A thesis, by definition, needs to be both compelling and arguable.  In other words, a good thesis will get some people excited and passionate to join your journey but will be alienating to others.  Your job isn’t to get all investors to like you — your job is to find investors who believe in your vision of the world.  This is hard to do, because as a fundraising entrepreneur, it’s tempting to want to tell a story that everyone will like.  But, I’m saying you shouldn’t — you should come up with a thesis that at least a few people love and most people completely disagree with.

5) Don’t differentiate on price

Lastly, don’t try to differentiate on price.  Price is icing on a cake but is not the cake itself.  Your product should be differentiated in other ways, and it’s nice if it’s cheaper.  But it shouldn’t only be cheaper.  That’s the easiest way for another company to compete with you.

Good luck!

Cover photo by Randy Fath

Happy 2017! Some shoutouts and new goals

Happy 2017!  I’m thankful to be surrounded by so many wonderful people and for good health in 2016.   I look forward to a great new year ahead of us.

Originally posted by 70s-80s-gifs

A few shoutouts and highlights from 2016:

1. Family

I feel so lucky and grateful to have such an amazing family.  Juggling our household schedules isn’t easy — especially with all my trips (Asia, Europe, LatAm, Canada, US) in 2016.  Those trips are a blast to be able to meet so many amazing driven entrepreneurs, but I realize it’s my family who ends up picking up the slack at home in order for me to do this.  I don’t ever forget that or take it for granted.

2. My 500 Startups family

2016 marked my first full year as an investor.  I never intended to go into VC. Honestly, I never thought I would work for someone else for so long (just passed my two year mark at 500)!  I’ve been fortunate to have had the chance to see, champion, and be a part of so many deals — probably more than most people will see over a lifetime, and it’s been amazing to learn so quickly from those.  Most of all, I’ve appreciated having the best team ever.  Teams and culture are the lifeblood of any company (including VCs), and it’s teams and culture that make people happy with their work — not compensation and not the day-to-day work itself.  I feel lucky to have such a great team.

3. My blog readers

My new year’s resolution for 2016 was to consistently blog at least once a week.  In the beginning, I started the blog because writing was cathartic for me and was a way for me to write down what I was advising founders already on a 1:1 basis.  I thought that keeping up the blog would be very difficult for me, but in the end, I missed just 4 weeks and ended this year with ~3k email subscribers.  Thank you for reading!

4. My Rejectionathon supporters

This year I started a half-day event called Rejectionathon to help entrepreneurs get over their fear of rejection.  It took me years to get comfortable with being rejected while I was selling ads for LaunchBit, and so I started this in order to help entrepreneurs develop a thicker skin more quickly.  At these Rejectionathons, entrepreneurs would receive a list of challenges and would run around trying to accomplish those challenges.  The challenges ranged from really tough tasks such as asking a stranger if he/she could help you figure out if your deodorant is working to easier tasks such as high-fiving a bunch of people in a restaurant or bar.  Special thanks to my Rejectionathon co-founder Thea Koullias, whose primary gig is being the CEO/founder at Jon Lou, who has helped me pull this all together.


These past couple of weeks, I’ve had some time to sit around and think about how I want to change things up in 2017.

A few goals and things I’m looking forward to this year on a professional front:

1. Focusing on earlier stage entrepreneurs

One of the things I’ve seen over the last couple of years is that a lot of seed investors start out investing in idea-stage entrepreneurs but as they build a track record and raise bigger funds, they tend to move downstream and invest more money in later stage seed companies.  My own employer 500 Startups is a great example of this.  Newer VCs, who don’t yet have a lot of deal flow then fill this void and the cycle repeats itself.  Because these investors don’t yet have a brand, entrepreneurs often don’t know they exist, and funding at this “pre-seed” level is very difficult to come-by.

When people say “there are more seed investors” than ever, usually they are talking about the ample seed dollars available for companies who are already thriving and growing.  But if you are just starting out and don’t yet have traction, this doesn’t really apply.  There are a couple of things that I aim to expand on in 2017 to help with this pre-seed stage and a couple more ideas that I have in the works that I’m not ready to announce yet.

A. Changing Rejectionathon

One of the issues that I see with so many pre-seed entrepreneurs (including myself when I was starting LaunchBit) is that so many people are incredibly timid in approaching activities that could lead to rejection.  Founders at this stage often are too afraid to sell products, establish business partnerships, or ask hard questions when fundraising because they are afraid of being rejected.  When we go through about 20 years of school, we never once learn how to develop a thicker skin, and yet, it is probably one of the most important skills you can develop in life.  This is what we set out to help entrepreneurs with via Rejectionathon.

Being able to get over rejection quickly to build momentum and traction is particularly important for the pre-seed stage because you just don’t have any runway to sit around and lollygag.  I’m going to talk more about this in a future blog post, but we are changing the nature of Rejectionathon.  It will still be a difficult set of challenges for entrepreneurs to tackle — to help them get over their fear of rejection.  But, we’re tweaking things so that it will be directly applicable to their businesses so that they can make progress on their startups while at a Rejectionathon.  In addition, in 2017, we tested the Rejectionathon concept domestically, but we plan to roll out more of these worldwide in 2017.

Our next one is in Mountain View on Sunday, January 29, 2017.  Use my code EYFRIENDS for 50% off.

B. Blogging 3x per week

In 2017, I am aiming to blog 3x per week.  Don’t worry, it won’t just be me blabbering more.  I still plan to only write about 1-2 posts per week with my own thoughts on fundraising.  But, towards the end of 2016, I started experimenting with other activities on my blog including “Ask a new investor” which is an interview series to highlight new investors and allow a curated group of entrepreneurs have a remote conference with them.  This is still in experimental stages, but the initial feedback from the first one was promising, so I plan to tweak this concept more and continue it in 2017.  The goal here is to illuminate more new investors (which is a fundamental problem at the pre-seed stage) and also make it easier for entrepreneurs to approach these people to better understand what they are looking for.

2. Focusing on high impact activities

Image credit: Business2Community

I’m sure many of you have seen this 2×2 matrix before.  This way of thinking drives how I structure my life, but it is so easy to fall into the trap of doing activities in #3.  This year, I aim to be better at this by doing these things:

A. Ignoring more emails

2016 was the first time I ignored a lot of emails.  At first I felt guilty.  (I still haven’t written back a whole bunch of people who applied to our seed program in the spring of 2016! 🙁 )  But the reality is that unfortunately, there just isn’t enough time in the day to respond to every email.  🙁

This has forced me to think about both my professional and personal email differently.  I now have more canned responses and automated emails than ever in order to write emails faster.  And I’m much more adamant about taking action right away on emails.  Either I respond or archive an email.  But, I shouldn’t let it sit around.  If an email sits around, it means I won’t respond to it ever, and I plan to be more decisive and proactive about that this year.

B. Moving more conversations to email

In addition, I now have gotten comfortable taking more initial conversations with people over email.  And then later moving them to phone if it makes sense to hash through the details.  A lot of my best mentors are people I’ve primarily talked with over email, and at first I had wondered just how helpful that could be compared to a phone call.  But, I’ve come to embrace email as a conversation medium and have learned that this allows both parties to respond whenever it’s convenient — even if it’s at 2am.  Phone calls, in contrast, need to be slotted for specific set times and don’t always fluidly work into schedules.

C. Outsourcing

I’ve written a bit before about outsourcing various personal chores.  In 2017, I hope to do more of this.

In addition, I’m always interested in playing with new tools to help save time.  I’m most interested in tools that can help me respond quicker to emails while on the go.  What I would really love is to be able to just quickly send a voice memo as a response to an email.  I don’t need a voice-to-text translator — I just want to be able to respond in some format quickly because that’s better than no response.

If you have any tools that help you with productivity, I would love to hear about them!

3. Exercising!

Lastly, I quit exercising for the latter 5 months of the year in 2016 because of my travel schedule.  In 2017, I’m going to resume swimming and hope to sign up for 1-2 lake races.  I never swam on a team as a kid and took up swimming just a few years ago because it’s a low impact exercise.  So I’m still a novice here and have even watched YouTube videos to improve my stroke!  In the past, the races in the Bay Area I’ve done and have really liked are the Tri Valley Masters Del Valle Open Water Festival in Livermore and the Splash and Dash Evening Series in the Stevens Creek Reservoir in Cupertino.  (The water is warm at both events and the best part is that they have hot dogs and pizza! 🙂 )

Wishing you a great year ahead – happy 2017!


Cover photo by on Unsplash

Why investors are like sheep (and how to herd them)

A fun little post for Halloween.  In many ways, a lot of investors are like sheep.  Not all.  But many.

Image courtesy of

Hopefully they are not like this:

Image courtesy of

I don’t know what sheep like to eat, so let’s say they like ice cream (I mean who doesn’t?) Let’s say you are selling ice cream cones, but other entrepreneurs are, too.  It can be easy for sheep to get paralyzed when deciding whom to buy ice cream from.  There are just so many options.


This can be frustrating if you’re trying to sell ice cream.

So you start by telling one sheep, “Hey, I have a limited amount of ice cream…wanna buy?”  Then you say the same thing to lots of other sheep.

Then, a bunch of sheep are now closer to your ice cream truck, but they are not buying your ice cream because they are still deciding whether they want your ice cream or someone else’s.  This is OK and perfectly normal.  At this point, there is no need to put a ton of pressure on any of the sheep until you have enough sheep moving your general direction.  This means you need to take a lot of initial meetings with a ton of sheep.

Images courtesy of 

Soon you’ve got some semblance of a herd around your ice cream truck, but no one is buying yet. So, you start to put more pressure on all of them: “Hey, I’m starting to have final conversations with a bunch of sheep.  If you are truly interested in my organic, gluten-free, tasteless ice cream, we really should talk in the next couple of days.”

At some point, you need to tell all the sheep, “I’m in final conversations with ~20 sheep about buying my ice cream but only have enough ice cream for ~10 sheep.  Can you let me know if you’re in or out?”

This is a risky move, but at some point you may just need to do this to round up as many sheep as you can.  In fact, your lasso (do people use that for sheep?) may end up missing everyone!  You may not end up with any sheep buying your ice cream, but if none of the sheep hovering around your ice cream truck is biting, you may just need to take that risk.

Sheepishly, this post may have made everything more confusing.  But, what do I know?  I’m not actually a sheep…


Happy Halloween!


Cover photo by Sam Carter on Unsplash